JP3544691B2 - 可溶性アニオン重合開始剤及びそれらからの生成物 - Google Patents

可溶性アニオン重合開始剤及びそれらからの生成物 Download PDF

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Publication number: JP3544691B2
Authority: JP; Japan
Prior art keywords: group; polymer; alkyl; carbon atoms; general formula
Prior art date: 1992-10-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

JP26947993A

Other languages

English (en)

Japanese (ja)

Other versions

JPH06199922A (ja

Inventor

デイビツド・エフ・ローソン

浩一森田

洋一小澤

マーク・エル・ステイヤー・ジユニア

良太藤尾

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Bridgestone Corp

Original Assignee

Bridgestone Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1992-10-02

Filing date

1993-10-04

Publication date

2004-07-21

1993-10-04 Application filed by Bridgestone Corp filed Critical Bridgestone Corp

1994-07-19 Publication of JPH06199922A publication Critical patent/JPH06199922A/ja

2004-07-21 Application granted granted Critical

2004-07-21 Publication of JP3544691B2 publication Critical patent/JP3544691B2/ja

2019-07-21 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

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239000003505 polymerization initiator Substances 0.000 title claims description 23
238000010539 anionic addition polymerization reaction Methods 0.000 title claims description 15
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 25
238000000034 method Methods 0.000 claims description 23
125000002947 alkylene group Chemical group 0.000 claims description 22
229930195733 hydrocarbon Natural products 0.000 claims description 22
239000004215 Carbon black (E152) Substances 0.000 claims description 21
150000002430 hydrocarbons Chemical class 0.000 claims description 21
239000003795 chemical substances by application Substances 0.000 claims description 17
125000004122 cyclic group Chemical group 0.000 claims description 7
125000003277 amino group Chemical group 0.000 claims description 5
150000002642 lithium compounds Chemical class 0.000 claims 1
229920000642 polymer Polymers 0.000 description 103
125000004432 carbon atom Chemical group C* 0.000 description 70
125000000217 alkyl group Chemical group 0.000 description 60
229920001971 elastomer Polymers 0.000 description 42
239000003999 initiator Substances 0.000 description 41
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 40
125000000753 cycloalkyl group Chemical group 0.000 description 37
239000000203 mixture Substances 0.000 description 31
229910052757 nitrogen Inorganic materials 0.000 description 31
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 28
-1 lithium amine Chemical class 0.000 description 28
125000003710 aryl alkyl group Chemical group 0.000 description 27
238000006116 polymerization reaction Methods 0.000 description 25
239000005060 rubber Substances 0.000 description 25
239000002904 solvent Substances 0.000 description 24
150000001412 amines Chemical class 0.000 description 23
239000006229 carbon black Substances 0.000 description 23
235000019241 carbon black Nutrition 0.000 description 23
125000003118 aryl group Chemical group 0.000 description 21
239000000178 monomer Substances 0.000 description 20
239000000806 elastomer Substances 0.000 description 17
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 16
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
125000000524 functional group Chemical group 0.000 description 16
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
150000002900 organolithium compounds Chemical class 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
239000007822 coupling agent Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
229920002554 vinyl polymer Polymers 0.000 description 13
239000011230 binding agent Substances 0.000 description 12
239000007795 chemical reaction product Substances 0.000 description 12
239000000047 product Substances 0.000 description 12
150000001993 dienes Chemical class 0.000 description 11
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 11
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 10
125000005037 alkyl phenyl group Chemical group 0.000 description 10
238000004519 manufacturing process Methods 0.000 description 9
150000004040 pyrrolidinones Chemical class 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
238000012360 testing method Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 7
238000006243 chemical reaction Methods 0.000 description 7
FRAKHUZTNLUGPB-UHFFFAOYSA-N 3,3,5-trimethyl-7-azabicyclo[3.2.1]octane Chemical compound C1C2NCC1(C)CC(C)(C)C2 FRAKHUZTNLUGPB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 6
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 6
ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 6
238000010168 coupling process Methods 0.000 description 6
238000005859 coupling reaction Methods 0.000 description 6
229910052744 lithium Inorganic materials 0.000 description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 5
229910052794 bromium Chemical group 0.000 description 5
229910002092 carbon dioxide Inorganic materials 0.000 description 5
239000001569 carbon dioxide Substances 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
125000001309 chloro group Chemical group Cl* 0.000 description 5
238000013329 compounding Methods 0.000 description 5
230000008878 coupling Effects 0.000 description 5
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
239000002994 raw material Substances 0.000 description 5
229910052710 silicon Inorganic materials 0.000 description 5
239000010703 silicon Substances 0.000 description 5
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
239000005062 Polybutadiene Substances 0.000 description 4
229910021627 Tin(IV) chloride Inorganic materials 0.000 description 4
239000006231 channel black Substances 0.000 description 4
229920001577 copolymer Polymers 0.000 description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
238000002156 mixing Methods 0.000 description 4
229920002857 polybutadiene Polymers 0.000 description 4
238000005096 rolling process Methods 0.000 description 4
HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 4
NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-n-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 3
150000001335 aliphatic alkanes Chemical class 0.000 description 3
125000003342 alkenyl group Chemical group 0.000 description 3
239000003963 antioxidant agent Substances 0.000 description 3
QXNDZONIWRINJR-UHFFFAOYSA-N azocane Chemical compound C1CCCNCCC1 QXNDZONIWRINJR-UHFFFAOYSA-N 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000009826 distribution Methods 0.000 description 3
230000000977 initiatory effect Effects 0.000 description 3
239000003607 modifier Substances 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
SDJHPPZKZZWAKF-UHFFFAOYSA-N 2,3-dimethylbuta-1,3-diene Chemical compound CC(=C)C(C)=C SDJHPPZKZZWAKF-UHFFFAOYSA-N 0.000 description 2
CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 2
RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
239000004594 Masterbatch (MB) Substances 0.000 description 2
229920000459 Nitrile rubber Polymers 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
230000003078 antioxidant effect Effects 0.000 description 2
UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 2
125000002619 bicyclic group Chemical group 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
239000005038 ethylene vinyl acetate Substances 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
238000009472 formulation Methods 0.000 description 2
229920001519 homopolymer Polymers 0.000 description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
238000010348 incorporation Methods 0.000 description 2
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
230000000379 polymerizing effect Effects 0.000 description 2
230000008569 process Effects 0.000 description 2
238000012545 processing Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
125000005504 styryl group Chemical group 0.000 description 2
239000000126 substance Substances 0.000 description 2
229910052717 sulfur Inorganic materials 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
229920003051 synthetic elastomer Polymers 0.000 description 2
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
150000005671 trienes Chemical class 0.000 description 2
AHAREKHAZNPPMI-AATRIKPKSA-N (3e)-hexa-1,3-diene Chemical compound CC\C=C\C=C AHAREKHAZNPPMI-AATRIKPKSA-N 0.000 description 1
PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 1
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
ZXHLQRSUVYZJGB-UHFFFAOYSA-N 1-(1-piperidin-1-ylethyl)piperidine Chemical compound C1CCCCN1C(C)N1CCCCC1 ZXHLQRSUVYZJGB-UHFFFAOYSA-N 0.000 description 1
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
OXUOGSGSDQETFG-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol 1-methoxy-2-(2-methoxyethoxy)ethane Chemical compound COCCOCCO.COCCOCCOC OXUOGSGSDQETFG-UHFFFAOYSA-N 0.000 description 1
DGPBVJWCIDNDPN-UHFFFAOYSA-N 2-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=CC=C1C=O DGPBVJWCIDNDPN-UHFFFAOYSA-N 0.000 description 1
FZLHAQMQWDDWFI-UHFFFAOYSA-N 2-[2-(oxolan-2-yl)propan-2-yl]oxolane Chemical compound C1CCOC1C(C)(C)C1CCCO1 FZLHAQMQWDDWFI-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
LICHZOBEUWVYSY-UHFFFAOYSA-N 3-azabicyclo[3.2.2]nonane Chemical compound C1CC2CCC1CNC2 LICHZOBEUWVYSY-UHFFFAOYSA-N 0.000 description 1
VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 1
JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
ZMGMDXCADSRNCX-UHFFFAOYSA-N 5,6-dihydroxy-1,3-diazepan-2-one Chemical compound OC1CNC(=O)NCC1O ZMGMDXCADSRNCX-UHFFFAOYSA-N 0.000 description 1
102100030310 5,6-dihydroxyindole-2-carboxylic acid oxidase Human genes 0.000 description 1
NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 1
LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 1
229920002943 EPDM rubber Polymers 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
244000043261 Hevea brasiliensis Species 0.000 description 1
101000773083 Homo sapiens 5,6-dihydroxyindole-2-carboxylic acid oxidase Proteins 0.000 description 1
101000823778 Homo sapiens Y-box-binding protein 2 Proteins 0.000 description 1
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
239000004809 Teflon Substances 0.000 description 1
229920006362 Teflon® Polymers 0.000 description 1
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229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
238000009825 accumulation Methods 0.000 description 1
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238000013019 agitation Methods 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
VYBREYKSZAROCT-UHFFFAOYSA-N alpha-myrcene Natural products CC(=C)CCCC(=C)C=C VYBREYKSZAROCT-UHFFFAOYSA-N 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
VYHBFRJRBHMIQZ-UHFFFAOYSA-N bis[4-(diethylamino)phenyl]methanone Chemical compound C1=CC(N(CC)CC)=CC=C1C(=O)C1=CC=C(N(CC)CC)C=C1 VYHBFRJRBHMIQZ-UHFFFAOYSA-N 0.000 description 1
229920001400 block copolymer Polymers 0.000 description 1
MTAZNLWOLGHBHU-UHFFFAOYSA-N butadiene-styrene rubber Chemical compound C=CC=C.C=CC1=CC=CC=C1 MTAZNLWOLGHBHU-UHFFFAOYSA-N 0.000 description 1
229920005549 butyl rubber Polymers 0.000 description 1
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239000004568 cement Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
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150000003950 cyclic amides Chemical class 0.000 description 1
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NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
238000004807 desolvation Methods 0.000 description 1
150000001983 dialkylethers Chemical class 0.000 description 1
239000012973 diazabicyclooctane Substances 0.000 description 1
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238000001035 drying Methods 0.000 description 1
KSCFJBIXMNOVSH-UHFFFAOYSA-N dyphylline Chemical group O=C1N(C)C(=O)N(C)C2=C1N(CC(O)CO)C=N2 KSCFJBIXMNOVSH-UHFFFAOYSA-N 0.000 description 1
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125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
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150000002513 isocyanates Chemical class 0.000 description 1
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239000006233 lamp black Substances 0.000 description 1
FJDQVJUXXNIHNB-UHFFFAOYSA-N lithium;pyrrolidin-1-ide Chemical compound [Li+].C1CC[N-]C1 FJDQVJUXXNIHNB-UHFFFAOYSA-N 0.000 description 1
239000000463 material Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
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CCRUHKGZAQXBKC-UHFFFAOYSA-N n-(2-methylpropyl)butan-1-amine Chemical compound CCCCNCC(C)C CCRUHKGZAQXBKC-UHFFFAOYSA-N 0.000 description 1
229920003052 natural elastomer Polymers 0.000 description 1
229920001194 natural rubber Polymers 0.000 description 1
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
125000001979 organolithium group Chemical group 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
150000002978 peroxides Chemical class 0.000 description 1
238000013031 physical testing Methods 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920001084 poly(chloroprene) Polymers 0.000 description 1
239000004848 polyfunctional curative Substances 0.000 description 1
229920001195 polyisoprene Polymers 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
229920005604 random copolymer Polymers 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
230000009467 reduction Effects 0.000 description 1
238000010074 rubber mixing Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
238000007493 shaping process Methods 0.000 description 1
229920002379 silicone rubber Polymers 0.000 description 1
239000004945 silicone rubber Substances 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
230000003381 solubilizing effect Effects 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
239000005061 synthetic rubber Substances 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
239000004636 vulcanized rubber Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F36/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F36/02—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F36/04—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds conjugated
- C08F36/06—Butadiene
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02T—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO TRANSPORTATION
- Y02T10/00—Road transport of goods or passengers
- Y02T10/80—Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies
- Y02T10/86—Optimisation of rolling resistance, e.g. weight reduction

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
Polymerization Catalysts (AREA)
Compositions Of Macromolecular Compounds (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Tires In General (AREA)

JP26947993A 1992-10-02 1993-10-04 可溶性アニオン重合開始剤及びそれらからの生成物 Expired - Lifetime JP3544691B2 (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US07/955,582 US5329005A (en)	1992-10-02	1992-10-02	Soluble anionic polymerization initiators and preparation thereof
US955582		1992-10-02

Related Child Applications (1)

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JP2003417031A Division JP2004169040A (ja)	1992-10-02	2003-12-15	可溶性アニオン重合開始剤及びそれらからの生成物

Publications (2)

Publication Number	Publication Date
JPH06199922A JPH06199922A (ja)	1994-07-19
JP3544691B2 true JP3544691B2 (ja)	2004-07-21

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Application Number	Title	Priority Date	Filing Date
JP26947993A Expired - Lifetime JP3544691B2 (ja)	1992-10-02	1993-10-04	可溶性アニオン重合開始剤及びそれらからの生成物
JP2003417031A Pending JP2004169040A (ja)	1992-10-02	2003-12-15	可溶性アニオン重合開始剤及びそれらからの生成物
JP2006318877A Expired - Lifetime JP4241809B2 (ja)	1992-10-02	2006-11-27	ゴム組成物及びタイヤ
JP2006318874A Expired - Lifetime JP4241808B2 (ja)	1992-10-02	2006-11-27	ゴム組成物及びタイヤ
JP2006318872A Expired - Lifetime JP4241807B2 (ja)	1992-10-02	2006-11-27	官能化されたポリマー及びその製造方法

Family Applications After (4)

Application Number	Title	Priority Date	Filing Date
JP2003417031A Pending JP2004169040A (ja)	1992-10-02	2003-12-15	可溶性アニオン重合開始剤及びそれらからの生成物
JP2006318877A Expired - Lifetime JP4241809B2 (ja)	1992-10-02	2006-11-27	ゴム組成物及びタイヤ
JP2006318874A Expired - Lifetime JP4241808B2 (ja)	1992-10-02	2006-11-27	ゴム組成物及びタイヤ
JP2006318872A Expired - Lifetime JP4241807B2 (ja)	1992-10-02	2006-11-27	官能化されたポリマー及びその製造方法

Country Status (6)

Country	Link
US (1)	US5329005A (fr)
EP (2)	EP0832903B1 (fr)
JP (5)	JP3544691B2 (fr)
CA (1)	CA2107621C (fr)
DE (2)	DE69333870T2 (fr)
ES (2)	ES2244988T3 (fr)

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1992
- 1992-10-02 US US07/955,582 patent/US5329005A/en not_active Expired - Lifetime
1993
- 1993-09-22 EP EP97121948A patent/EP0832903B1/fr not_active Expired - Lifetime
- 1993-09-22 ES ES97121948T patent/ES2244988T3/es not_active Expired - Lifetime
- 1993-09-22 DE DE69333870T patent/DE69333870T2/de not_active Expired - Lifetime
- 1993-09-22 DE DE69330418T patent/DE69330418T2/de not_active Expired - Lifetime
- 1993-09-22 EP EP93115255A patent/EP0590491B1/fr not_active Expired - Lifetime
- 1993-09-22 ES ES93115255T patent/ES2160584T3/es not_active Expired - Lifetime
- 1993-10-04 CA CA002107621A patent/CA2107621C/fr not_active Expired - Fee Related
- 1993-10-04 JP JP26947993A patent/JP3544691B2/ja not_active Expired - Lifetime
2003
- 2003-12-15 JP JP2003417031A patent/JP2004169040A/ja active Pending
2006
- 2006-11-27 JP JP2006318877A patent/JP4241809B2/ja not_active Expired - Lifetime
- 2006-11-27 JP JP2006318874A patent/JP4241808B2/ja not_active Expired - Lifetime
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Also Published As

Publication number	Publication date
JP4241808B2 (ja)	2009-03-18
JP4241809B2 (ja)	2009-03-18
ES2244988T3 (es)	2005-12-16
EP0590491B1 (fr)	2001-07-11
DE69330418T2 (de)	2001-11-08
EP0832903A3 (fr)	1998-05-27
CA2107621C (fr)	2005-08-02
EP0832903B1 (fr)	2005-09-14
DE69330418D1 (de)	2001-08-16
CA2107621A1 (fr)	1994-04-03
ES2160584T3 (es)	2001-11-16
JP2004169040A (ja)	2004-06-17
JP2007084834A (ja)	2007-04-05
JPH06199922A (ja)	1994-07-19
US5329005A (en)	1994-07-12
JP4241807B2 (ja)	2009-03-18
EP0832903A2 (fr)	1998-04-01
DE69333870T2 (de)	2006-06-22
EP0590491A2 (fr)	1994-04-06
EP0590491A3 (en)	1994-05-18
DE69333870D1 (de)	2005-10-20
JP2007146164A (ja)	2007-06-14
JP2007092079A (ja)	2007-04-12

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Publication	Publication Date	Title
JP3544691B2 (ja)	2004-07-21	可溶性アニオン重合開始剤及びそれらからの生成物
US5723533A (en)	1998-03-03	Soluble anionic polymerization initiators and products therefrom
JP4157170B2 (ja)	2008-09-24	環状アミン含有アルキルリチウム化合物および重合におけるそれらの使用
JP3998160B2 (ja)	2007-10-24	環状アミン含有アミノアルキルリチウム化合物およびそれらを用いて得られるポリマー類
US5332810A (en)	1994-07-26	Solubilized anionic polymerization initiator and preparation thereof
CA2058562C (fr)	2003-05-27	Etain contenant des elastomeres et produits a proprietes d'hysteresis reduites
EP0593049B1 (fr)	1997-01-02	Amorçeurs de polymerisation anionique et des polymères à basse hystérésis en résultant
US5616704A (en)	1997-04-01	Solubilized anionic polymerization initiators
JPH072916A (ja)	1995-01-06	アニオン重合開始剤およびそれから得られる低下したヒステリシスを示す製品
JPH08225604A (ja)	1996-09-03	アニオン重合開始剤およびそれらを用いて得られる低下したヒステリシスを示す製品
EP0626278B1 (fr)	1999-01-13	Amorçeurs de polymérisation anionique solubilisés et produits en résultant
US5959048A (en)	1999-09-28	Soluble anionic polymerization initiators for preparing functionalized polymer